28122-84-1Relevant articles and documents
Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols
Singh, Pallavi,Peddinti, Rama Krishna
, (2021/02/22)
Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].
Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation
Zhao, Bin,Fu, Yao,Shang, Rui
, p. 9521 - 9526 (2019/11/28)
Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.
Kinetics and Mechanism of the Aminolysis of S-Phenyl Thiobenzoates
Lee, Ikchoon,Shim, Chang Sub,Lee, Hai Whang
, p. 769 - 793 (2007/10/02)
Kinetic studies on the nucleophilic substitution reaction of S-phenyl thiobenzoates with anilines have been carried out at 55.0 deg C.Effects of substituents in the nucleophile(X), substrate(Y) and leaving groups(Z) are analyzed in terms of Hammett's and Broensted's coefficients, ρi and βi and cross-interaction constants ρij and βij where i and j denote X, Y or Z.The sign of ρXZ (or βXZ) is positive, and accordingly, the transition state(TS) variations with the substituents are consistent with those predicted by the potential energy surface diagram; the magnitude of ρx(βx) and ρxy decreases with a better leaving group, and that of ρz and βz decreases with a stronger nucleophile leading to an earlier TS, in agreement with a normal Hammond effect.The larger magnitudes of ρXY, ρYZ and βXZ suggest that the reaction proceeds by an associative SN2 mechanism.A greater kH/kD value (1.0) is observed with deuterated aniline nucleophiles for a stronger nucleophile and a better leaving group, supporting the earlier TS proposed on the basis of the cross-interaction constants.The inverse secondary kinetic isotope effects obtained preclude involvement of any four-center TS or base catalysis by aniline.